Synthesis and biological evaluation of glycosylated psoralen derivatives

• Published in: Tetrahedron Vol. 68; no. 12; pp. 2598 - 2606
• Main Authors: Chen, Chao-Yue, Sun, Jian-Guo, Liu, Fei-Yan, Fung, Kwok-Pui, Wu, Ping, Huang, Zhi-Zhen
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 25.03.2012; Elsevier
• Subjects: Analytical, structural and metabolic biochemistry; Antineoplastic agents; Antioxidant activity; Antioxidants; Antiproliferative activity; Antiproliferatives; Biological; Biological and medical sciences; Biotechnology; Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides; Carbohydrates. Nucleosides and nucleotides; Chemistry; Chemistry, Organic; Derivatives; Dna, deoxyribonucleoproteins; Exact sciences and technology; Fundamental and applied biological sciences. Psychology; General aspects; Glycosylated psoralen derivatives; Heterocyclic compounds; Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives; Human; Medical sciences; Nucleic acids; Organic chemistry; Pharmacology. Drug treatments; Physical Sciences; Preparations and properties; Science & Technology; Synthesis; Synthesis (chemistry); Tetrahedrons; Synthesis; Antiproliferative activity; Antioxidant activity; Glycosylated psoralen derivatives; CELLS; ANTIOXIDANTS; ANALOGS; ANGELICA-DAHURICA; CANCER; ENZYME TUMOR-THERAPY; INHIBITION; COUMARIN GLYCOSIDE; PRODRUGS; FURANOCOUMARINS; Antineoplastic agent; Copper II; Mild operating conditions; Tripeptide; Oxygen heterocycle; Polyphenol; Glycoside; Oxidation; Chemical synthesis; Glutathione; Human; Oside; Glycosylation; Malignant tumor; Antioxidant; Biological activity; Pyrogallol; Cell line; Photoinduction; Sulfur peptide; DNA; Psoralen derivatives; Cancer
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/j.tet.2012.01.090

A novel route for the efficient synthesis of a target psoralen moiety, 4,4′-dimethylxanthotoxol, has been developed, which need only four steps using cheap pyrogallol as a starting material. Subsequently, a range of new glycosylated psoralen derivatives were synthesized in good yields with simple procedures and mild reaction conditions. The experiment of biological activity shows that some of the glycosylated psoralen derivatives have antiproliferative activities against human cancer cell lines. A strong photo-induced antiproliferative effects were found under UVA. All of the glycosylated psoralen derivatives exhibited antioxidant activities against the oxidation of DNA induced by Cu2+/glutathione (GSH). Further experiment also demonstrates that the introduction of sugar moieties in some glycosylated psoralen derivatives can improve their antioxidant activities significantly. [Display omitted]